


Until the Grapes Grow Dust

by Sinna



Category: Newsies - All Media Types, Newsies!: the Musical - Fierstein/Menken
Genre: Alternate Universe - Modern Setting, Aromantic, Lots of OCs - Freeform, M/M, Nonbinary Character, Oscar is aro and gay and trans and a mess, Other, Trans Female Character, Trans Male Character, more detail in relevant chapter notes, most of them are trans, there's something going on between Oscar and Jack but its' not romantic, warnings for dubcon and self harm, wine forgery is fascinating I did RESEARCH for this fic
Language: English
Status: Completed
Published: 2017-07-29
Updated: 2017-09-28
Packaged: 2018-12-08 07:15:20
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 8,564
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11641614
Author URL: https://archiveofourown.org/users/Sinna/pseuds/Sinna
Summary: Oscar Delancey is just trying to put his younger brother through college without falling back into old habits. It's harder than expected.(Or, the fic where Oscar gets involved with wine forgery)





	1. Riesling

**Author's Note:**

> I wrote this purely for myself, but a couple people said they were interested, so here it is. I went into this imagining it as a modern day Great Gatsby, but it... didn't turn out that way. See what you think. 
> 
> The full story is completed (and about 8,000 words), so you can expect quick updates. 
> 
> Also if anyone wants to read up about wine forgery just hit me up in the comments. I have plenty of recommendations.

Oscar drew the black tie a little tighter around his neck and finally faced his reflection in the slightly grimy bathroom mirror. To his surprise, he looked… okay. Good, even.

He’d let Jessie do his hair earlier and, while it meant he bore an unfortunate resemblance to a hipster, that was kind of the idea for tonight.

He turned to and fro, wincing at the way his chest stuck out. Realistically, he knew it wasn’t that bad, but it had been a long time since he’d worn anything as tight as this slightly too small dress shirt. Aggressively, he pulled on the suit jacket and buttoned it.

Better.

He squared his shoulders and turned away.

“That’s a nice getup!” a voice yelled across the apartment as he left the bathroom. Morris was in the kitchen, carefully arranging row upon row of pizza rolls on a plate.

“Did you eat any actual food yet?” Oscar asked, ignoring the comment about his outfit.

“Pizza rolls are actual food,” Morris insisted.

“Not remotely.”

“Fuck you.”

He almost made it out the door.

“So what’s with the fancy outfit?” Morris asked.

“It’s for a job,” Oscar told him, reaching for the doorknob.

“What kind of job?” Morris’ voice took on a sharper tone.

Oscar sighed and turned back to face his brother. “A friend of a friend knows a guy who works at a snazzy restaurant. There’s some sort of event there tonight and they need extra hands. That’s it.”

“What kind of event?” Morris asked suspiciously. “Which friend?”

“It’s some sort of fancy wine tasting event,” Oscar explained. “Completely above the board. And sure to be plenty of rich people dropping big tips. Can I go now, _mother_?”

Morris recoiled, but it was a distraction from the friend question. Oscar didn’t feel too bad as he dashed out the door.

Normally, he would just walk anywhere he needed to go, but this was far even for him, and he didn’t exactly have the time to walk halfway across New York City. So he swallowed the lump in his throat and took the subway, trying not to wince every time someone brushed up against him.

 

He rarely came to this part of the city. Everything was overpriced and he always felt like everyone was judging him. Well, more than usual. He found the back door Jeannine had told him about and slipped inside.

A large group of people stood in the middle of the kitchen. At the center of the crowd, a tall woman in an exquisitely pressed pantsuit was speaking. Oscar stepped into the circle, listening closely as she finished giving instructions to the assembled servers. They scattered when she was done.

Noticing Oscar, she gestured for him to come closer, frowning as she examined his outfit.

“You’re the kid Jeanie sent?” She asked.

Not trusting his voice, he nodded. She adjusted his jacket, then, seemingly satisfied, she began ordering him around.

The night went smoothly after that. Oscar hated the job, but money was money. If he was going to get Morris through college, he couldn’t afford to be picky about where the money came from. Or, well…

“Excuse me?”

Oscar was on his way back into the kitchen when a tall redhead stepped into his path.

“Sir?”

“Might I make a small request of you?” the man asked.

A familiar green flashed as the man casually tucked his hand in his pocket. Oscar’s eyes were instantly drawn.

“I’m at your service,” he assured the man.

“Excellent. Would you mind gathering up all these bottles for me? Just deliver them to my chauffeur. She’s out in the parking garage. She’ll have the rest of your payment.”

With that, the man slipped a hundred-dollar bill and a business card into his hand. Oscar’s heart skipped a beat as he tucked the cash and card into his pocket.

“A pleasure doing business with you,” he said.

The man smiled.

“Likewise.”

Oscar ducked back into the kitchen. The empty wine bottles were piling up on a section of the counter. He made a beeline for them.

“Oscar, right?”

He pulled up short as the woman’s voice reached him.

“Yes, ma’am?”

“Can you take those bottles out back and smash them? We don’t want any forgers getting their hands on them.”

It felt like a sign. “Yes, ma’am.”

He managed to fit about a quarter the bottles into one of the large crates next to the door, and resigned himself to making multiple trips.

He carefully slipped outside and made his way to the parking garage.

A dark-haired woman in a suit was leaning against a very nice black car, smoking a cigarette. A very nice car, he noted, with plenty of room in the trunk.

“Are those for Mr. A?” she asked, as Oscar approached.

He shifted the crate to one hip and took a look at the business card in his pocket. _Tyler Anders_.

“That’s right.”

“This can’t be it,” she observed, looking through the crate with distaste.

“There’s plenty more in the kitchen,” Oscar told her. “I’ll get the rest of it. But first I want to know how much I’m getting for this. I’m supposed to be smashing these bottles.”

“I’ve got five hundred bucks in the car for you,” she told him nonchalantly.

It confirmed Oscar’s suspicions. There was something more than just an eccentric rich dude going on here. But outwardly he shrugged and went back for more bottles.

 

By the end of the night, he’d carried seven crates of wine bottles out to where Shea was still smoking those damn cigarettes and he had six hundred-dollar bills tucked in his pocket, next to the check with his official pay for the evening.

He was waiting outside the restaurant’s front entrance when Tyler Anders left with a group of friends. Oscar waited a moment, then ran after them.

“Mr. Anders!” he called.

Anders turned around, raising an eyebrow as he saw Oscar.

“There’s been a small discrepancy with the bill,” Oscar lied. “Would you come back inside with me and sort things out?”

Anders’ eyes hardened, just for a moment, before he smiled and waved his friends along.

“I’m sure this will just be a moment.”

He followed Oscar back inside. Once they were out of view, all pretense of joviality dropped away.

“How much more do you want?” he asked peevishly. “Shea paid you, didn’t she?”

“She did.” Oscar confirmed. “Five hundred bucks. I want a thousand. Or I tell the head of the restaurant what you paid me to do.”

Anders reached for his checkbook.

_Gotcha_ , Oscar thought.

“And I want in,” Oscar added.

Anders raised an eyebrow. “What do you ‘want in’ on, as you so quaintly put it?”

Oscar swallowed down his annoyance.

“You’re too quick to bribe me,” he explained. “No one just drops a thousand bucks on someone like me unless you think I could really hurt you. No matter how rich you are. You’re not using the bottles for art projects.”

“What do you think I’m using them for?” Anders asked, a little too guarded to come off as truly nonchalant.

“Wine forgery, I’d guess,” Oscar replied, trying to match his tone.

“If you’re right, what possible use could I have for a skinny college boy?”

“I never went to college,” Oscar told him. “Too busy scamming folks out of their money so my little brother and I could eat. I want 10% of what you make on those bottles I got for you, and a steady job that at least looks legal on paper. The percentage is negotiable, the job is not.”

Anders frowned.

“Meet me at the address on my card. Noon tomorrow. Dress nicely and don’t be late.”

Oscar grinned. “A pleasure doing business with you.”

Anders scowled.

 

As he made his way home, he texted Aunt Abigail.

_I’m keeping the clothes for another day. Job interview at noon._

By the time he got home, she’d texted back.

_It’s your head on a platter if you don’t get them back by two. We need the jacket for the matinee._

He smiled and let himself in.

Morris was asleep curled up on the couch. Again.

Oscar sighed and shook him by the shoulder. After a few moments, Morris shook himself awake.

“You’re home.”

“I know you’re dying to get rid of me,” Oscar teased. "But you'll have to put up with me for a little longer."

“Don’t joke about that,” Morris snapped.

He was always more honest when he’d just woken up.

“You should go to bed,” Oscar said. “Actual bed.”

“You should come home at reasonable hours,” Morris shot back.

“I got a job offer,” Oscar told him.

Morris scrambled up to his feet.

“What?”

“We’ll talk in the morning.”

It was an evasion and they both knew it, but Morris was still half asleep and didn’t call him on it. Oscar figured, knowing Morris’ normal Saturday routine, he could be out and back before Morris even woke up. He’d even have time to drop the clothes back at Medda’s theater.

...probably.


	2. Chardonnay

**Summary for the Chapter:**

> Oscar gets a new job.

The address on Tyler Anders’ business card was a charming penthouse apartment in one of the nicer New York neighborhoods. Anders didn’t even invite Oscar inside.

Instead, he met him outside the door and shepherded him into a car - the same car from the night before. Shea sat in the driver seat, an unlit cigarette held loosely between her lips.

“So where are we going?” Oscar asked.

“I have a lovely estate outside the city,” Anders remarked calmly.

Oscar glanced out the window as Shea began driving.

“Any reason you can’t offer me a job inside the city?” he wondered.

“You were the one who blackmailed me into giving you a job,” Anders retorted coldly. “Anyway, how did a kid without a college education get a job at such a nice restaurant and why do you need a new one?”

“I didn’t,” Oscar explained blithely. “They needed some extra hands for that event last night. I’m friends with a woman who sings there sometimes. She told them I had experience with catered events.”

“Do you?” Anders asked.

He seemed genuinely curious.

“Sure, if you count two opening parties at an off-broadway theatre when I was fifteen.” Oscar grinned.

“You have a lot of experience bending the truth, don’t you?” Anders sounded begrudgingly impressed.

“You ain’t even heard the half of it,” Oscar told him.

It wasn’t even a lie.

Anders leaned forward.

“Shea. Turn the car around. I believe I may have found a better use for… what’s your name?”

“Oscar. Oscar Delancey.”

 

“Boy, it’s 2:05. Jessie goes on in three minutes. Get that jacket off your shoulders right this second.”

Oscar stripped the jacket off and kissed his aunt on the cheek.

“I told you I’d have it back on time.”

She ruffled his hair and grabbed the jacket out of his hands.

“I am bringing this backstage so our leading lady doesn’t have to go on without a vital part of her costume and then I will be right back and you will explain to me why you’re trying so hard to ruin my career by giving me gray hairs.”

Oscar laughed and took a seat on one of the lobby’s plush benches. True to her word, Aunt Abigail was back in a few minutes.

“Did you get Jessie the jacket?” he asked.

“You’ll live,” she told him. “This time. Now tell me about this job interview of yours. When did you get an interview for the type of job you need a suit for?” 

“Last night. Met a guy at the thing Jeanine got me into. I just got a job as his new personal assistant.”

“You’re sleeping with him?” Abigail asked.

She folded her arms over her chest. Oscar shrugged.

“Not yet. He’s nice enough on the eyes, but I don’t trust him.”

“Since when did you make good choices about sleeping with guys?”

It wasn’t like he could argue with her, but he still mustered a look of wounded pride.

She laughed. “Just be careful, okay?”

“Aren’t I always?”

They both knew he was joking.

“Go watch the show. There’s an empty aisle seat in row J.”

Oscar slipped into the theater and found the seat his aunt had mentioned. The show was halfway through the [second scene], and Jessie, as usual, was killing it. The jacket was securely on her shoulders.

_Twelfth Night_ wasn’t his favorite, but Medda and her girls always put on a good show, and this was no exception. Especially with Jessie as Viola.

 

She had been so excited when she got the role. Oscar remembered her giggling into a bottle of champagne the night she got the call. He also remembered her crying on the couch later that night as the nerves hit her.

“Why can’t you come be Sebastian with me, Os?” she’d asked between sniffles. “I want you up on that stage with me. I want someone who doesn’t think I got this role because of my mother.”

“No one thinks Medda just handed you the role on a silver platter,” Oscar had told her, rubbing her back. “And beside, I don’t think we could pass for siblings, much less twins.”

“And you don’t wanna be in the company anymore.”

When he was little, he’d wanted to be up on that stage with his aunt, yeah, but now…

“I’m not a girl,” Oscar had pointed out.

“You know very well that ‘All-female’ really means anyone who’s not a cis guy to Mom,” Jessie had replied. “She’d cast you. I know you can act.”

“You know it’s not Medda I’m worried about. It’s everyone else. I don’t want anyone thinking I’m just a girl in drag.”

“But it’s ART, Oscar,” she had tried to explain. “It’s okay if they’re confused.”

 

Oscar tried to brush the memory away. She’d apologized for the conversation in the morning, but it had still been uncomfortable. She found freedom in putting her gender on display. Her bio proudly identified her as a transgender woman, and she loved playing girls who disguised themselves as men. Oscar wasn’t sure he’d ever feel that way. He put a lot of effort into making sure people believed he was just another cis guy.

 

As the play went on, Jessie noticed him in the audience. He could tell when she did, because suddenly all her asides were addressed to him. After curtain call, he snuck backstage and found her dressing room. He knocked lightly, then – finding the door unlocked – poked his head inside.

“Sorry. I forgot flowers.”

“Hey loser!” She crossed the room to hug him. “How’d you like the show?”

“Brilliant, as always,” he told her. “You were perfect.”

He noticed a watercolor taped to the wall. The style was familiar.

“Jack came by already?” he asked.

She followed his gaze to the painting. Jack had captured her mid-monologue, and the colors almost leapt off the page.

“He came first preview,” she said. “Dropped that off yesterday for opening night.”

Oscar didn’t know quite how to continue that conversation. Jessie grimaced.

“You two still aren’t talking?”

He shook his head. She sighed. “You’re both idiots.”

“I know.”

There were a lot of things Oscar regretted.  Alienating one of his former best friends was something that probably should have been higher on the list.

But honestly? He mostly just felt bad about getting Jessie caught in the middle of things.

 

Morris was awake – and waiting for him – when he got home. As usual, he cut right to the chase.

“Job offer?”

“Good morning to you too,” Oscar deflected.

“Are you getting back involved with-”

“No!”

Morris settled down a little.

“What is it then? You never told me you were looking for anything new.”

“That rich people party. This one guy took a shine to me I guess and offered me a position as his personal assistant.”

“And by personal assistant you mean…?”

“Personal assistant. Organizing meetings and answering phone calls and stuff.”

“And he’s not just trying to get you in bed?”

“What is it with you and Aunt Abby? Is it really so impossible to think I could get a job without seducing the guy? I blackmailed him.”

“I can’t tell if you’re joking or not.”

“I didn’t blackmail him that much,” Oscar promised. “Nothing that could be used as evidence in court.”

“If you end up in jail, I’m going to kill you.”

“I’m sure there’ll be a line.”

Morris frowned.

“I wish you’d stop doing stuff like this.”

“If I had better options, I’d take them.”

And that was it. They’d had this argument more times than Oscar could count. He couldn’t deny that he’d done some stupid things. Hell, he’d been doing stupid things most of his life to take care of Morris. Maybe Morris was right, and he should let Morris take on more of the responsibility now that he was eighteen.

But his job at the liquor store plus Morris’ part time job at his school’s coffee shop only just covered their rent plus Morris’ tuition, and Morris barely had enough time for homework as it was. If there was a way he could make things better, he was going to take it.

“I promise I know what I’m doing.”

“No, you don’t.”

Oscar shrugged. “Okay, I don’t. But it’s a risk I’m willing to take, and you can’t stop me.”

 

**Notes for the Chapter:**

> Oscar and Jack as former best friends is word of actor canon and it's a dynamic I love playing with.


	3. Merlot

**Summary for the Chapter:**

> Oscar's first day at work goes about as terribly as he expected

Oscar spent half of the money he’d already made from Tyler Anders on business clothes. Morris frowned when he saw Oscar all dressed up for the second time in as many days. He was still viewing everything about this with suspicion, and Oscar couldn’t really blame him. He’d tucked the receipts from the new clothes at the bottom of his sock drawer, just in case.

This time, when he reached Anders’ apartment, Shea opened the door. She frowned, but stepped aside to let him in.

“Mr. Anders is in his office,” she said. “I’ll show you the way.”

She led him through the apartment. The word that came to Oscar’s mind was “chic”.

Anders looked up as they entered. He frowned slightly when he saw Oscar.

“Did no one ever teach you how to properly size a shirt?” he asked.

Oscar scowled and fought the urge to cross his arms over his chest.

“What’s that supposed to mean?”

“The shirt you were wearing yesterday. It was too small. It’s why I picked you. Figured you’d be the most susceptible to a bribe. The one you’re wearing now is too big.”

“Well between my parents abandoning me at age eight, a series of shitty foster parents, and moving out on my own at eighteen… No, no one ever taught me.”

“I’ll give you my tailor’s number. Just tell him to send the bill to me.”

“No!” Oscar winced at the way his voice sounded – tight and too high.

Anders raised a single perfect eyebrow.

“I know a tailor who will do it cheap for me,” Oscar offered. “Works for a professional theater, so she’ll get it right. I’m not taking your charity.”

He was relieved when Anders didn’t press for details.

“Very well. I’ll deal with your ill-fitting clothes for today.”

It won’t be accepted after today, was the unspoken condition. Oscar wondered how much Aunt Abigail would kill him for this.

 

“So, how’s the job going?” his Aunt asked as she deftly tucked and folded fabric. Oscar tried not to breathe as the pins danced close to his skin.

“Fine, besides the fact that he wants my clothes tailored,” he told her. “And the fact that he’s always judging everything I do. And the fact that he’s an insufferable prick.”

“That bad?” Abigail remarked, through a pin gripped in her teeth.

“The money’s good though.”

“How legal is this really?”

“I told you- ow!”

When Aunt Abigail stabbed someone with a pin, it was never an accident. Oscar sighed.

“Okay, it’s not entirely legal. But this isn’t like last time. I promise.”

She frowned.

“I’m serious. I’m not in danger. Legal or otherwise.”

Instead of answering, she shifted his position so she could better reach the bottom hem.

“Working late again, Abby?”

Medda Larkin swanned into the room in her dressing gown, and Abigail set down her pins.

“More like taking advantage of your excellently stocked costume shop to do some tailoring for my good-for-nothing nephew.”

 Medda turned her attention to Oscar.

“Causing trouble for your aunt again, boy?”

Oscar shrugged. “Guess I can’t help it.”

Medda laughed. “You never could. What is it this time?”

“My new employer threw a fit about my clothes and tried to send me to his tailor.”

Medda frowned at that.

“Abby, I’ll pay you overtime for this.”

“I’m already paying her,” Oscar insisted.

“Well then we’ll both be paying her, won’t we?”

When Medda got like this, there was no stopping her. Oscar thought she would have solved all the world’s problems if anyone had ever given her the chance to do so.

Aunt Abigail went back to the business of pinning Oscar’s shirt. Medda went over and put the kettle on the stove. There was a familiar comfortable silence as the two women worked that drained the last of the tension from Oscar’s shoulders.

Aunt Abigail finally finished pinning the shirt and motioned for Oscar to take it off. He didn’t bother putting his t-shirt back on. Medda had given him his first binder. There was nothing to hide from her. She scanned his skin for injuries or new scars, but it was little more than a habit and they both knew it. There was rarely anything new these days.

She set a mug of tea in front of him. “So, do you want to tell me why you haven’t come around except when you need favors from Abby? I’m seeing Morris more often than you these days.”

Oscar wanted to deny it, but it was true. There had been a time when he’d spent every spare moment he had in the theater. But recently…

“Just haven’t had the chance,” he mumbled.

“For almost two years?”

“It’s complicated.”

She frowned. “This isn’t facebook, Oscar. You’re gonna have to give me more than that.”

“I don’t want to talk about it.”

“I’ve let you get away with not talking about it for too long.”

“It’s none of your business.”

“Jessie’s upset, Jack looks like he wants to punch something every time he hears your name, and Abby’s lending you costumes between performances. I think it is my business.”

Oscar flinched.

“Jack has a right to be mad at me.”

“Is that so?”

Oscar looked away. He’d already said too much.

“I didn’t mean to hurt Jessie,” he said finally. “I promise. I’ll fix it. Somehow.”

“You’d better.”

Thankfully, she left it at that. For the rest of the night, the conversation stuck to safe topics. Medda complained about the theater’s finances and rambled about their new intern, Abby regaled them with stories of day to day life in the costume shop. Oscar told them about Morris’ adventures in college.

It was the happiest he’d felt in a long time.

**Notes for the Chapter:**

> Oscar's aunt working at Medda's theater is also word of actor canon
> 
> Also Medda is an out and proud trans woman like her daughter in case that wasn't clear


	4. Champagne

**Summary for the Chapter:**

> A Business Trip

“Here, take my card to the Starbucks around the corner and get me some coffee. Large mocha latte for me and, uh, Shea? You want anything?”

She looked up from where she was studying an auction listing.

“Iced black coffee please.”

“And get yourself whatever you want,” Anders added.

Oscar pocketed the card with a sigh and left the apartment. He’d been working for Anders for three days, and it had been nothing but running minor errands like this, with Anders throwing money around like it was going out of style. He thought he should be happy about it. He was making a ton of money for very little work, and so far he hadn’t had to do anything illegal, besides bringing Shea those bottles. He could maybe be charged as an accomplice, but they’d have to prove he knew what Anders was doing.

Maybe it was time to admit that his motives for blackmailing Anders into a job hadn’t been as pure as he liked to pretend. Stupid and dangerous as it was, he’d missed the rush of pulling off a con. He’d wanted to get back into the game of deceit and easy money. The game where he never had to be himself.

Stupid, stupid-

He shook the thought away. He just needed to keep things as they were. Ignore his stupid head and just keep things safe. Morris was already worried enough as it was.

He quickly ordered Anders and Shea’s coffees, as well as a coffee for himself. He tossed in an order of cookies and tried to convince himself it was because Anders had said “whatever you want” and not because he was testing what the guy would let him get away with.

He came back, and Anders and Shea were whispering over the auction listing. Anders looked up and grinned.

“Oscar! Perfect timing! How would you like to go to North Dakota?”

Oscar raised an eyebrow. “What’s in North Dakota?”

“An estate sale. Which happens to include an extensive wine cellar. Nothing too good, so none of the serious collectors will be there, but if we change out the labels we could make some real money.”

Oscar couldn’t help a grin. “When do we leave?”

“You leave tomorrow. I already bought you a plane ticket. I’ll also give you a card with two million. That should cover the wine, plus any expenses. Call me if you need more.”

It seemed way too good to be true.

“You’re trusting the guy who blackmailed you, and told you he has a habit of ripping off rich people, with two million dollars?’ he asked suspiciously. “Unsupervised?”

“If you were planning to steal the money and run off, you wouldn’t have asked me that,” Anders pointed out. “Besides, you’ll make that and more if you just stick with me and we both know it.”

Well, he wasn’t wrong.

He was still an annoying prick though.

 

Morris was not happy to hear that Oscar would be getting on a plane the next morning.

“You know this is a huge red flag, right?” he said as he paced their living room floor.

“What do you mean?”

“He’s probably testing you somehow. Seeing how much he can get away with.”

“Or he just found out about a good deal and can’t go out there himself. He’s wildly rich. They’re all eccentric.”

“Or murderers,” Morris pointed out.

He nearly tripped over a chair as he turned too quickly. Oscar unconsciously reached out to steady him.

“I told you. I’m going to take the risk.”

Morris pulled away from him.

“You almost died last time you took a risk like this!” he shouted.

Oscar winced. “You promised you wouldn’t bring that up again.”

“I never thought you’d be stupid enough to get yourself back in the same situation!”

“It’s completely different!” Oscar insisted.

He turned away sharply, not waiting for Morris’ response.

“I need to go pack.”

“You’re an asshole,” Morris yelled at his retreating back.

“Tell me something I don’t know,” Oscar shot back.

 

He was still in a huff as he waited in the airport early the next morning. Anders’ credit card felt like lead in his wallet. He’d already spent six dollars from that new card on coffee, and it hadn’t helped. If anything, it had made him more jittery.

A security guard walked past on his right, speaking into his comm, and for a minute he was fourteen again. The sensation of panicky fast breaths, constricted by a too-tight sports bra, threatened to overwhelm him, before he forced his attention back to the present. No one was after him. He was wearing a binder, not a sports bra, and it fit perfectly. This was all in his head.

He was almost relieved when his flight started boarding, until he saw the inside of the airplane. It was tiny and cramped and oh damn this was going to be hell.

“Do you need help finding your seat, sir?” a woman asked him with a brilliant customer service smile.

“Er, actually, yes,” Oscar admitted.

“May I see your ticket?”

He handed over his phone. Her eyebrows raised a few millimeters before that carefully cultivated customer service look snapped back into place.

“You’re seated here in the front, in our first class section.”

So preoccupied by the low ceilings and the rush of people, Oscar hadn’t noticed the small section of seats near the front.

“You could have boarded earlier, you know,” the flight attendant told him. “First class gets priority boarding.”

Oscar shrugged.

“I was busy.”

She hesitated for a moment.

“No offense, but you don’t seem like the type of guy who travels first class.”

Oscar smiled.

“Normally, I’m not the type of guy to travel anywhere I can’t walk.”

“So what happened? Large inheritance?” she asked, pointing him to a large, comfortable seat.

“Very rich employer,” he told her, sitting down.

She looked impressed.

The seat was, in fact, very comfortable, and better yet it kept him away from strangers. For the first time, Oscar felt a little bit grateful to Anders.

If it had been intentional, not just the man’s weird desire to show off his wealth in every possible way, Oscar might have even started to like him.

 

There was something slightly addicting about stepping into a room where no one had ever met him before, even if everyone was looking down on him. Oscar was officially here as “A Representative of an Anonymous Bidder,” and he was mostly ignored, except by a tall teenage girl clearly there with her parents and clearly mostly interested in the looks of outrage they sent her every time she spoke to him.

Her name was Elvira – “Please call me Elvis” – and she was actually pretty cool. Apparently, rich people watched Star Wars too, and she had some pretty solid opinions about Anakin Skywalker. She also dropped some nice hints about how to get ahead in the bidding, which he was extremely grateful for. Apparently, she’d been going to these with her parents for years, and she couldn’t help picking some things up, despite her carefully cultivated air of distaste.

In return, Oscar managed to work a casual mention of nonbinary identities into one of their conversations. She couldn’t hide the way her eyes lit up. He’d either helped someone find their identity, or given a bored rich girl one more tool to shock her parents, and he didn’t care which.

 

Other than that, North Dakota was uneventful. Oscar got the wines Anders sent him for, and had half a million dollars left over. He resisted the urge to spend that money in the airport. Not yet. Not until he figured Anders out.

When he got off the flight back to New York, at 7:30 in the morning, Morris was waiting for him.

“Hey.” He wasn’t quite sure where they stood.

“I came to make sure your dumb ass made it back,” Morris said.

Oscar couldn’t help a smile. “All in one piece.”

He spun around, as if Morris might need visual confirmation. Morris sighed and pulled him into an awkward sort of half hug.

“You’re such a shit brother.”

“I try.”

“No more business trips for- for the next month. At least. Got it?”

“Got it,” Oscar agreed.

Oscar decided he could treat Morris to breakfast on Anders’ credit card. It totally counted as a business expense.

 

Anders, as it turned out, was very pleased with Oscar’s trip to North Dakota.

“I expected you to need more,” he admitted with a grin, pacing his spacious office.

Oscar shrugged. “I’ve picked up a few things here and there. You want the card back?”

“Keep it,” Anders offered. “I’ll put more on it next time I send you to an auction. Feel free to spend what’s left in the meantime.”

Oscar sat bolt upright.

“You’re just giving me half a million bucks?” he asked dubiously.

“Think of it as a bonus. I’m gonna turn what you bought into at least six million. I figure you’ve earned it.”

“You’re crazy,” Oscar muttered.

“I’m also very very rich,” Anders pointed out. “So I’m allowed to be crazy.”

 

On the way home, he stopped by Medda’s theater. The person in the box office was unfamiliar, tall and dark haired. Maybe the new intern Medda had mentioned. Davin or something? The kid looked slightly terrified as Oscar approached.

“You got a name?” Oscar asked. “Pronouns?”

“Davey,” the intern squeaked. “He/him. Can I help you? I mean, I can’t uh sell you a ticket right now because I’m just the intern, but I can answer questions, and Demi will be back in like ten minutes, so, uh…”

“What about accepting donations?” Oscar asked.

He could see Davey thinking about it.

“I mean technically I can’t, you should really wait for Demi, but if you’re in a hurry, I guess I could figure something out?”

Medda had been right. Davey was smart, for all his anxiety. Never turn down someone offering you money. Although Oscar wasn’t sure what he’d done to look like the kind of person who was in a hurry. But whatever. He didn’t want to wait for Demi anyway. She knew him.

He shoved a manila envelope through the window. Davey stared at it.

“Careful. That’s ten thousand dollars.”

Davey dropped the envelope like it had burned him.

“Do you want to leave a name?” he asked, after taking a minute to compose himself.

“I’ve always wanted to be an anonymous donor,” Oscar said with a grin.

He could feel Davey staring after him as he walked away.

**Notes for the Chapter:**

> Davey isn't cis thank you for your time


	5. Sauvignon Blanc

**Summary for the Chapter:**

> Medda is done with Oscar's shit

Medda called him later that night.

“Don’t scare my interns.”

“Hello to you too, Miss Medda.”

Morris looked up from across the room, before too casually turning his attention back to a game of Candy Crush on his phone.

“I’m serious, Oscar,” Medda said. “I had to send Davey home early today.”

“I didn’t mean to scare him that much,” Oscar told her.

“What possessed you to drop ten thousand dollars cash off in an envelope? We take checks for a reason.”

“I didn’t want anyone to trace it to you,” Oscar admitted softly.

“Oscar. Baby. What have you gotten yourself into?”

“Nothing. It’s not dangerous. I mean it. It’s just… I won’t feel safe letting anything personal slip until I have this guy figured out. That’s all.”

“Oscar, you remember what happened last time?”

“This isn’t like what happened last time,” Oscar snapped.

“Then maybe you’d better stop being so secretive about it. You owe us that much.”

Oscar sighed. “I’ll come by Monday. You can interrogate me all you want then.”

“Deal.”

“So what was that about?” Morris asked, the second he hung up the phone.

“Medda’s sick of me keeping secrets.”

Morris rolled his eyes. “Aren’t we all?”

“You’re all just nosy,” Oscar snapped.

Morris jumped to his feet. “You don’t have the right to say that. Not with some of the shit you’ve pulled. We have every right to want to know what you’re up to so that we can be prepared for it to blow up in our faces.”

Oscar winced.

“Can’t you just trust that I know what I’m doing?”

“Not anymore.”

Oscar sighed.

“Fine. Wine forgery. That’s what I’m involved with. See? Low risk.”

Morris was staring. “You couldn’t have just said that?!”

“You didn’t need to know. It’s better if you don’t.”

“Cause no one ever needs to know you, right?”

Oscar could tell Morris was some kind of furious right now, but he couldn’t figure out what it was about.

“I’m sorry, I guess?”

Morris groaned. “You always think you have to do everything all by yourself. Keep everyone in the dark, until you’re so damn over your head that you don’t have any choice about it.”

“What’s the problem with that?” Oscar asked, crossing his arms. “It’s better that way.”

“I hate you so much,” Morris said, but there was a hint of fondness to it.

Oscar recognized the tone. They weren’t done with this, not by a long shot, but Morris was willing to let it go for now.

 

“You can stay late tonight, right?” Anders asked.

He’d promised to talk to Medda, but, well, he wouldn’t mind putting that off.

“How late?” he asked suspiciously. “For what?”

 “Just an hour or two,” Anders said. “I want to go over some finances and I could use a second pair of eyes.”

“Sounds good,” Oscar agreed.

 

In the end, the two of them were buried in forms for a solid three and a half hours. Oscar started off going slowly to take up time so he could put off visiting Medda, but he was quickly drawn in. He’d always liked numbers, and there was something addicting about finding and sorting the patterns in Anders’ finances.

At nine pm, Anders finally stopped them.

“That’s way more than I was planning to do,” he admitted, brushing nonexistent specks of dust off his jacket. “You have a good head for this.”

Oscar shrugged. “I’ve always liked numbers.”

“Will you be able to get home okay?” Anders asked. “I could have Shea drive you.”

Oscar hesitated. It was an appealing alternative to the subway.

Anders didn’t wait for confirmation of Oscar’s decision.

“Shea!”

She wandered into the room a few moments later, rubbing sleep from her eyes.

“Yeah?” She saw Oscar and suddenly straightened. “Oh, you’re still here.”

“Will you take him home?”

“No problem, boss,” she said, in a tone of voice that conveyed that it was very much a problem.

“Never mind. I’ll call a cab,” Oscar offered.

“It’s fine,” Shea assured him. “Let’s go.”

 

Oscar waited until they were inside the car to start asking questions.

“So who are you really?” he asked.

“What’s that supposed to mean?” she asked.

“You and Anders. What are you two? He’s obviously not just your boss. Are you sleeping with him or something?”

Shea made a face.

“Ew! No. He’s my kid brother.”

“Your brother?”

She nodded. “Surprise, or whatever. He wanted to keep it from you. I don’t know why. Probably trying to impress you or something. He likes looking cool.”

“So you’re the brains of the operation?” Oscar asked, the pieces starting to come together.

“I guess you could say that,” she admitted. “Ty hasn’t got much of a head for business.”

“I figured that out tonight,” Oscar remarked.

That coaxed a bit of a smile from her.

“Are you two adopted?” Oscar asked.

Tyler, who looked like he’d stepped out of an Irish folk legend, didn’t exactly look related to her.

“Thanks for not automatically assuming I’m the adopted one,” she said.

Oscar shrugged. “My parents abandoned me and my brother when I was ten. I know what it’s like in the system.”

“I don’t. I actually am the adopted one though. His family adopted me when I was a baby,” Shea explained. “Mom thought she was infertile. Two years later, miracle boy showed up.”

“And you’re still bitter about it?” Oscar guessed.

“I was. Until, well, let’s not get too deep into my family history. No offense, but I don’t trust you yet.”

“The feeling is mutual,” Oscar assured her.

“That’s fair.”

They drove the rest of the way in a surprisingly comfortable silence. She dropped him at the address he gave – two streets away from his real one – and he waited until she was gone to walk home.

 

He realized he’d had his phone in airplane mode only when Morris mentioned that Medda had called. Shit. Sure enough, once he turned it off, he had three texts and a missed call.

He quickly called back.

“Hey, uh, Medda?”

“You’d better have a damn good explanation, boy.”

“I was working late and my phone was on airplane mode?”

Medda’s end of the line was silent.

“I really did mean to text you,” Oscar promised, hoping the words didn’t sound as hollow as they felt.

“Look, Jessie’s got the afternoon off next Monday. She and Jack are going to meet for lunch. I invited you along.”

“Medda!”

“No one’s making you go,” Medda pointed out. “Just think about it.”

Oscar sighed. There were a thousand excuses on his tongue, but Medda hung up before he could voice any of them.

“You’re in trouble,” Morris sing-songed.

“I’m not,” he insisted.

“You’re going to lunch with them, aren’t you?” Morris asked.

Oscar hesitated only a moment. “I guess so.”


	6. Moscato

**Summary for the Chapter:**

> In which there are many important conversations

**Notes for the Chapter:**

> Aren't y'all impressed by my ability to take forever posting something I had already finished writing? But this is the final chapter. I'm starting on a Javid fic set in this universe and I've got some ideas for a sequel, so keep an eye out, but this is it for now.
> 
> Also heads up this is the chapter where all the warnings in the tags become relevant. More detailed warnings in the end note.

It was Thursday night when Tyler kissed him for the first time.

They were supposed to be working on finances again, but for the past hour it had been Oscar working while Anders showing off his skills at guessing the years of some of the less valuable wines he had stored in his cellar. Officially, he called it “refining his palate,” but Oscar knew better.

A half full bottle of wine came down on his papers.

“Dammit, Anders!” Oscar muttered. “I have a job to do.”

“Have a drink,” Anders offered, his voice slightly slurred.

“I don’t drink,” Oscar informed him curtly.

A lie, but not one he felt any guilt about.

“Come on, I feel like shit drinking alone,” Anders whined. “Oscaaaar.”

Oscar sighed and raised the bottle to his lips, intending to merely fake a sip, but then he met Anders’ eyes. The man wasn’t nearly as drunk as he was acting.

Finally, here was a game he knew the rules to. Just enough wine to pretend they weren’t responsible for their actions. And then… well…

Oscar downed half of the remaining wine and licked his lips. Anders was on him in moments. Oscar kissed back, reveling in the roughness of it. Anders pinned his wrists to the arms of the chair, and Oscar didn’t fight it. If Anders’ hands were holding him down, they weren’t anywhere else.

He dropped the nearly empty bottle on the floor. The sound of it shattering on the wooden floor was like music.

“I could have used that bottle,” Anders pointed out.

“Buy another one,” Oscar suggested.

Oscar had slept with people who would have hit him for that. He was almost disappointed to find out Anders wasn’t the type.

“You’re lucky you’re a hell of an accountant, or I’d be taking that out of your paycheck.”

“Shut up, Anders.”

“If you’re going to sleep with me, call me Tyler.”

“Fine.”

“You are going to sleep with me, right?”

“No, I was just going to let you kiss me and pin me to a chair and then run out on you,” Oscar snapped sarcastically.

Tyler frowned, but – thankfully – was more interested in sex than psychoanalysis and let whatever he was thinking slide in favor of pressing his teeth against Oscar’s throat. Oscar tilted his head to the side in an unspoken invitation.

Inevitably, of course, Tyler reached for the top buttons of his shirt. Half on instinct, Oscar grabbed his hand to stop him.

“Oscar?”

“There’s something you should know… before this goes any further…”

Tyler frowned.

Oscar always hated this. With trembling hands, he unbuttoned his shirt.

“I…”

“You’re trans,” Tyler observed.

Oscar started. “What? – yes.”

“Okay.”

“Okay?”

“Dude, Shea’s nonbinary. I get it. Can we get back to the part where I get to fuck you?”

Oscar kissed him hard.

 

An hour later, Oscar stood under the scalding hot water of Tyler’s shower, trying to rinse the feel of the man’s fingers from his skin and cataloguing the new bruises.

Surprisingly – or perhaps not – it was Jack’s voice echoing in his head.

_What the hell have you gotten yourself into, Oscar?_

Jack had been talking about a different set of bruises, but it was all the same, really.

It wasn’t the bruises – blossoming in red and purple along his neck, his wrists, his thighs – that hurt, that lingered on his skin like an invisible rash. It was the moments Tyler was gentle: the kisses without teeth, the soft caresses.

Jack had never understood that.

Tyler had tried to pull him closer after they were both finished, and Oscar could still feel the weight of his arm. He’d escaped with the excuse of a shower, but he couldn’t stay in here forever.

He did stay until the hot water ran cold. Finally, he stepped out and dried himself off, clumsily pulling his clothes back on.

When he stepped out of the bathroom, Tyler was thankfully asleep.

Oscar spared a single glance for the pajamas folded neatly on a chair before sneaking out.

 

Shea was watching Netflix in the main room. She paused her show the moment she heard Oscar.

“You can just stay the night,” she offered.

“My brother will be waiting up,” Oscar explained.

Knowing Morris, it was probably even true.

“Want a ride?”

Oscar hesitated, then nodded. Shea grabbed her keys.

 

“He told me you’re nonbinary,” Oscar mentioned, once they were in the car.

“What?!”

Oscar looked deliberately out the window, watching her reaction in the glass.

“I told him I’m trans.”

“You’re trans?”

“I’ve been on T since I was fifteen.”

“I never would have guessed,” she said, with a small smile.

“Would you prefer other pronouns?” Oscar asked.

“They/them would be nice,” they admitted. “But only when it’s just us, or just us and my brother.”

“Got it.”

 

He got home at 1:30 am. Morris was still awake. He took one look at Oscar’s wrinkled clothes and wet hair and frowned.

“Oh god you slept with him.”

“Good to see you too,” Oscar snapped. “I’m an adult. I can fuck anyone I want to.”

“Doesn’t mean you should,” Morris pointed out. “Sleeping with your boss is like number one on the list of things not to do if you want to keep your job.”

“Why is my sex life any of your business?”

“Am I not allowed to worry about you?”

“I wish you’d stop,” Oscar said.

“Fuck you.”

Morris stormed off to his room.

Oscar collapsed on his bed in still-rumpled clothes and finally let himself sleep.

 

Seeing Jack for the first time in two years shouldn’t have felt like a punch in the gut.

It did.

From the look on Jack’s face, he had the same reaction. Jessie looked between the two of them.

“Should I leave you two alone to talk?” she asked.

“Maybe,” Jack said.

“No!” Oscar insisted at the same time. If she left, he couldn’t count on himself to get through this.

The three of them sat down in a booth in the back corner of the coffee shop. Jessie looked pointedly at her phone, clearly determined not to get involved.

“I see you haven’t changed a bit,” Jack remarked, eyes on Oscar’s neck.

Oscar fought the urge to adjust his shirt to hide the bruises.

“And you’re still as judgmental as ever,” Oscar retorted.

“Is that what you think this is?” Jack asked incredulously.

“Well then what is it?” Oscar asked. “I told you I never wanted us to be exclusive.”

“I never cared about that,” Jack insisted, arms crossed and a blush spreading across his face.

Translation: he cared, but he tried very hard not to. Then why…?

“I just couldn’t stand around while you tried to get yourself killed.”

Oscar nearly doubled over at the accusation.

“I wasn’t-”

“Weren’t you?” Jack’s tone was softer now. “I’ve known you since we were both five, Oscar. You think I never noticed the pattern? You never used a razor blade. You just found guys twice your age who would hurt you.”

Oscar winced and looked at Jessie. She’d gone pale, but she wasn’t trying to argue with Jack. That said a lot.

“Is that really what everyone thinks?” Oscar asked quietly.

Jessie looked up from her phone.

“Are we wrong?”

Oscar wanted desperately to say no, but the words wouldn’t come, a hundred little excuses he’d made to himself suddenly crumbling away now that someone said it aloud. He curled into himself, trying to remember how to breathe.

“Oscar?”

He felt a hand on each of his shoulders.

“Shit. You okay?” Jack asked.

“Fine,” Oscar choked out.

After a few long seconds he managed to pull himself back together.

“I’m really fine,” he lied. “I wore my binder for too long yesterday.”

“We don’t have to talk about it just yet,” Jack offered.

“There’s nothing to talk about.”

He knew that neither of them believed him, but… maybe that was okay.

 

By the end of lunch, the three of them were laughing. It felt like the past two years had never happened. Jack was leaning against Oscar’s side, and Jessie was sitting across the table, leaning forward as she giggled, relating her favorite backstage mishaps.

“Shoot!” Jack checked his phone. “My lunch break was over ten minutes ago. I gotta go!”

He jumped up and threw his arms around Jessie quickly. “Break a leg, Jess!”

He turned to Oscar and, after a moment’s hesitation, pulled him into a similar hug.

“Take care of yourself, okay?” he murmured into Oscar’s shoulder.

And then he was gone.

“Was that so hard?” Jessie asked, turning to face Oscar.

“More than you can imagine,” Oscar insisted. “But… thanks.”

“You okay? With… what Jack said?”

Oscar hesitated. “I’ll get there,” he said finally, opting for the truth.

She reached for his hand.

“I know you will.”

“Need me to run lines with you?” he offered.

"As a matter of fact..."

 

“You’re late,” Tyler observed.

Oscar shrugged and picked up a folder from Tyler’s desk, idly flipping through it. He was just starting to make some calculations when he felt Tyler come up behind him. He tensed, numbers muddling together in his mind.

“I can’t concentrate with you looking over my shoulder,” he snapped.

“You can do the accounting later,” Tyler suggested. “Shea’s out for the next few hours.”

His lips brushed against the back of Oscar’s neck.

Oscar almost gave in. He wanted to. A day ago he would have. But… well… he couldn’t get Jack’s words out of his head. Or the way Jessie had looked at the ground in silent agreement.

“Stop,” he said quietly.

“Oscar?”

Thankfully, Tyler took a step back.

“I have a job to do.”

“Well, if that’s all you’re worried about, I am your boss,” Tyler pointed out. “Hell, I should be giving you a bonus for this.”

“I didn't sleep with you for the money,” Oscar snapped back.

“Whoa! I wasn’t-”

“I know,” Oscar said.

“I thought we had a thing.”

“We did. It’s over.” His voice was carefully flat.

“Can I ask why?”

Oscar didn’t look at him.

“Because I’m not what you want, and you’re too much of what I want, and it’s not good for either of us.”

“Huh?”

This was harder than he’d anticipated. Dealing with people usually was.

“Nevermind. Just… no more.”

“Okay…”

Tyler abruptly turned and walked out of the room. Oscar breathed a small sigh of relief. He still felt empty inside, but it wasn’t like that ever changed.

He pulled out his phone and texted Jessie.

_u have a show tomorrow, right?_

The response was immediate.

_Yeah. Jack’s coming to that one._

He only hesitated for a moment.

_get me a ticket?_

_No problem. You’re paying for it though._

_that’s fair._

He had a lot of people he needed to make things up to.

**Notes for the Chapter:**

> Detailed warnings  
> \- Dubcon: two characters have consensual sex but they're slightly intoxicated and also one of them is basically using it as a form of self harm (the other is not aware)  
> \- Domestic violence: same scene as previous, implications that a character has been physically abused by previous partner(s)  
> \- If you want to skip those two (or the sex in general, although it's mostly fade to black), go to the paragraph beginning "Shea was watching Netflix in the main room."  
> \- Self harm: discussion of character's self harming/suicidal tendencies, there's really no way to skip this


End file.
